A row of houses with a mountain in the background.

Pleasant Valley Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Pleasant Valley Vacation

The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or choose someplace else — our packages are all about you. If your trip to Pleasant Valley includes some sightseeing, visit renowned attractions like Marist College, Vassar College and Culinary Institute of America. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Pleasant Valley vacation is easy with Expedia.

Top Pleasant Valley vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A rooftop terrace with outdoor seating, a city view, and a brick building.
    Jan 13 - Jan 16

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,692
    CA $984
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • A historic building with ornate architectural details, multiple floors, and illuminated windows.
    Jan 15 - Jan 17

    The St. Regis New York + Flight

    Manhattan
    2 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,470
    CA $1,311
    per traveller
    found 1 day ago
    The St. Regis New York
  • A modern outdoor seating area with a sofa, armchairs, and ottomans, a glass door leading to a bedroom, and potted plants.
    Feb 4 - Feb 7

    The Langham, New York, Fifth Avenue + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $3,716
    CA $2,105
    per traveller
    found 13 hours ago
    The Langham, New York, Fifth Avenue
  • A building with a sign that reads 'CHEMISTS' CLUB' and a flagpole with an American flag.
    Dec 17 - Dec 21

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    9.4/10 - Exceptional (569 reviews)
    "Noise in my room and toilet didn’t work"
    Reviewed November 11, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop EWR - YYZ • Nonstop
    CA $3,558
    CA $2,196
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • A modern kitchen with white cabinetry, a stainless steel stove, and a herringbone-patterned floor.
    Jan 15 - Jan 19

    LGA AIRPORT + Flight

    Queens
    4 nights
    2.0 star property
    10/10 - Exceptional (2 reviews)
    "The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future. "
    Reviewed December 24, 2025
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,789
    CA $1,126
    per traveller
    found 4 hours ago
    LGA AIRPORT

Discover the most popular places to visit in Pleasant Valley

Innisfree Garden

10.0/10 (2 reviews)
Explore the great outdoors at Innisfree Garden, a lovely green space in Pleasant Valley. Wander the riverfront in this family-friendly area.
See properties

Pleasant Valley Hotel Deals

A hotel entrance with a brick facade, a glass door entrance, and a paved walkway.

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG
2.5 star property
11.6 km from Pleasant Valley
8.6 out of 10, Excellent, (1,002 reviews)
The price is CA $138
CA $160 total
includes taxes & fees
Dec 1 - Dec 2
Holiday Inn Express Poughkeepsie by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Pleasant Valley

Frequently Asked Questions

How much does a Pleasant Valley vacation package cost?

You'll find cheap prices from CA $984 on Expedia for your Pleasant Valley escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Pleasant Valley costs.

What are the cheapest months to go to Pleasant Valley?

To pick up cheap Pleasant Valley vacation packages, plan your getaway outside of peak periods such as public holidays. You'll typically find better availability and lower prices for flights and hotels.

How many days is enough for Pleasant Valley?

We'd suggest booking a Pleasant Valley vacation for at least 3 days. This gives you enough time to check off popular sights including James Baird State Park and Vassar Golf Course, and check out neighbourhoods like Arlington and Fairview. You might even be able to slot in a day trip or two from Pleasant Valley.

How to find the best Pleasant Valley package deals?

Landing a cheap Pleasant Valley package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Pleasant Valley package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.

Is it cheaper to book a Pleasant Valley vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Pleasant Valley vacation by choosing your favourite type of stay, airline and car class.

How to plan a trip to Pleasant Valley?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Pleasant Valley.
  2. Set your budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Pleasant Valley. Then, choose a hotel that works with your budget, whether that's a low-cost option or a swankier retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Pleasant Valley. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, lock in the right Pleasant Valley vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.